Antidepressant medication
Trazodone Trade names Desyrel, Trittico, others[ 1] Other names AF-1161 AHFS /Drugs.com Monograph MedlinePlus a681038 License data
Dependence liability Low[ 2] Addiction liability Low-Moderate[ 2] Routes of administration By mouth ATC code Legal status
Bioavailability By mouth : 65%[ 7] [failed verification ] Protein binding 89–95%[ 8] Metabolism Liver (CYP3A4 , CYP2D6 , CYP1A2 ?)[ 11] [ 17] [ 12] [ 18] [ 19] Metabolites mCPP Tooltip meta-Chlorophenylpiperazine [ 9] Onset of action By mouth : 1 hour (Tmax )[ 10] Elimination half-life • Trazodone (IR ): 4–15 hours[ 11] [ 12] [ 13] [ 14] • Trazodone (ER ): 9–13 hours[ 15] [ 12] [ 13] • mCPP Tooltip meta-Chlorophenylpiperazine : 3–16 hours[ 11] [ 12] [ 14] [ 16] Excretion Urine : 70–75%[ 7] Feces : 21%[ 7]
2-{3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl}[1,2,4]triazolo[4,3-a ]pyridin-3(2H )-one
CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.039.364 Formula C 19 H 22 Cl N 5 O Molar mass 371.87 g·mol−1 3D model (JSmol ) Melting point 87 °C (189 °F)
Clc4cccc(N3CCN(CCCN1/N=C2/C=C\C=C/N2C1=O)CC3)c4
InChI=1S/C19H22ClN5O/c20-16-5-3-6-17(15-16)23-13-11-22(12-14-23)8-4-10-25-19(26)24-9-2-1-7-18(24)21-25/h1-3,5-7,9,15H,4,8,10-14H2
Y Key:PHLBKPHSAVXXEF-UHFFFAOYSA-N
Y
(verify)
Trazodone , sold under many brand names,[ 1] is an antidepressant medication,[ 20] used to treat major depressive disorder , anxiety disorders , and insomnia .[ 20] It is a phenylpiperazine compound of the serotonin antagonist and reuptake inhibitor (SARI) class.[ 21] [ 22] The medication is taken orally .[ 20]
Common side effects include dry mouth , feeling faint, vomiting, and headache.[ 20] More serious side effects may include suicide , mania , irregular heart rate , and pathologically prolonged erections .[ 20] It is unclear if use during pregnancy or breastfeeding is safe.[ 23] Trazodone also has sedating effects.[ 24]
Trazodone was approved for medical use in the United States in 1981.[ 20] It is available as a generic medication .[ 20] In 2022, it was the eighteenth most commonly prescribed medication in the United States, with more than 27 million prescriptions.[ 25] [ 26]
^ a b "Trazodone" . Drugs.com . Retrieved 9 February 2019 .
^ a b Hubbard JR, Martin PR (2001). Substance Abuse in the Mentally and Physically Disabled . CRC Press. p. 26. ISBN 978-0-8247-4497-7 .
^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)" . nctr-crs.fda.gov . FDA . Retrieved 22 October 2023 .
^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023 .
^ Cite error: The named reference Desyrel FDA label
was invoked but never defined (see the help page ).
^ Cite error: The named reference Trazodone FDA label
was invoked but never defined (see the help page ).
^ a b c Truven Health Analytics, Inc. DrugPoint System (Internet) [cited 2013 Oct 1]. Greenwood Village, CO: Thomsen Healthcare; 2013.
^ "Trazodone" . DrugBank . Retrieved 7 June 2015 .
^ Preskorn SH, Stanga CY, Feighner JP, Ross J (2012). Antidepressants: Past, Present and Future . Springer Science & Business Media. pp. 68–. ISBN 978-3-642-18500-7 .
^ "MicroMedex DrugPoints – Trazodone" . Pharmacy Choice . Retrieved 20 April 2017 .
^ a b c Cite error: The named reference pmid10379419
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^ a b c d Cite error: The named reference pmid22115401
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^ a b Cite error: The named reference pmid23192413
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^ a b Cite error: The named reference pmid20173086
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^ Cite error: The named reference pmid26678742
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^ Schatzberg AF, Nemeroff CB (2017). The American Psychiatric Association Publishing Textbook of Psychopharmacology (5th ed.). American Psychiatric Pub. pp. 460–. ISBN 978-1-58562-523-9 .
^ Cite error: The named reference pmid31379379
was invoked but never defined (see the help page ).
^ Cite error: The named reference pmid9836023
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^ Lemke TL, Williams DA (2012). Foye's Principles of Medicinal Chemistry . Lippincott Williams & Wilkins. p. 615. ISBN 978-1-60913-345-0 .
^ a b c d e f g "Trazodone" . The American Society of Health-System Pharmacists. 17 March 2021. Retrieved 24 December 2021 .
^ Stahl SM (2008). Stahl's Essential Psychopharmacology: Neuroscientific Basis and Practical Applications . Cambridge University Press. p. 567. ISBN 978-0-521-85702-4 .
^ Lemke TL, Williams DA (2008). Foye's Principles of Medicinal Chemistry . Lippincott Williams & Wilkins. p. 586. ISBN 978-0-7817-6879-5 .
^ "Trazodone Use During Pregnancy" . Drugs.com . Retrieved 7 January 2018 .
^ British national formulary: BNF 69 (69th ed.). British Medical Association. 2015. pp. 257–58. ISBN 978-0-85711-156-2 .
^ "The Top 300 of 2022" . ClinCalc . Archived from the original on 30 August 2024. Retrieved 30 August 2024 .
^ "Trazodone Drug Usage Statistics, United States, 2013 - 2022" . ClinCalc . Retrieved 30 August 2024 .